Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1.[NH4+].[Cl-]>C1COCC1>[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:21]3([OH:24])[CH2:22][CH2:23][C:18]4([O:25][CH2:15][CH2:16][O:17]4)[CH2:19][CH2:20]3)=[CH:3][CH:4]=2)=[N:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 8 g of 2-(4-bromophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole (31.5 mmol) in 15 ml of anhydrous THF is poured dropwise onto 956 mg of Mg (39.3 mmol) in such a way as to maintain the mixture at the reflux temperature and the mixture is refluxed for 2.5 hours. The mixture is cooled to room temperature and a solution of 5.41 g of 1,4-cyclohexandione monoethyleneacetal (34.65 mmol) in 20 ml of anhydrous THF is added to it dropwise. The mixture is stirred at room temperature for 1.5 hours and then at reflux temperature for 1 hour. The mixture is poured into 500 ml of a 10% NH4Cl solution and extracted with ethyl acetate. The organic phase is dried and, after filtration, the solvent is evaporated off under reduced pressure. The residue is crystallized in ethyl acetate. The product of the title is obtained in the form of a white solid.
Workup
- temperatureto maintain the mixture at the reflux temperature
- temperaturethe mixture is refluxed for 2.5 hours
- temperatureat reflux temperature for 1 hour
- extractionextracted with ethyl acetate
- customThe organic phase is dried
- filtrationafter filtration
- customthe solvent is evaporated off under reduced pressure
- customThe residue is crystallized in ethyl acetate
- customThe product of the title is obtained in the form of a white solid
Sources & evidence
- ORD record
- ord-fbf95506f37f4ab1aab89c9847e6c956
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07419974B2
Linked notes
Loading…